Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 1: First Intimate Contract
Erotica Sex Story: Chapter 1: First Intimate Contract - I thought my old college friend Roger would be my first and last time as a whore, but Cupid made other plans. The Joker took advantage by messing with my guy’s biggest client. I had to get this done or jobs would be lost. This time it was the real thing, I had to whore for a stranger who was known to pay more for a girl going outside the rules. A lot more. He was a nice older man who wanted my ass, and as an extra surprise he brought some family! (All over 18.)
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Heterosexual Fiction Sharing Slut Wife Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Sex Toys Prostitution
As I thought of it for a moment, after all the doubts and surprises this had really gone well for me. Mr. G was an attractive older man (I would guess 60 years old), fit, powerful but friendly, not intimidating. Plus, he was paying me a great deal, so much that I knew there was another surprise coming my way. This was in addition to him putting his cock into me, both front and back. I figured that he would enjoy the evening much more than I would. But as long as I was here I might as well play a little.
We were both ready to go, we had removed our clothing and doused some of the bright lights. “Look, I don’t want to mess up your routine, you are in charge and I am willing ... but...”
He understood. “Is there something you like to do first? I see that there is. What do you suggest?”
I was honest. “Well as I said, I am no expert on oral, and I don’t want to rush things, but I must say that your ... well, it looks like something yummy to try ... a mouthful, just to taste.”
“Not many women I meet say such things to an older man,” he replied. “Nobody has used the word ‘yummy’ about me since ... well, I can’t remember when.”
“Well ... maybe when I am more experienced I will be different, but for now I am kind of curious to try it. So may I?”
He wanted to be clear. “My understanding is that your rules do not allow our lips to kiss, nor do they allow my lips to kiss your very beautiful, and delicious-looking, little slit, and they do not allow penetration in the back. But as we have agreed that we are not using any of those silly rules tonight ... so how about we both try the delights you suggest, because you look good to me too. Perhaps the 69 position with you on top? How does that sound?”
“I don’t know what to say, it seems I am getting the better part of that deal,” I replied with a smile as I moved towards the bed.
“In negotiations, I often find that is a good time to say ‘Yes’ to the other party,” he replied.
“Wise advice.”
He stretched himself out on the bed, then he bid my pussy into that very promising position above his face.
I realized that this man’s charm had disarmed me very completely. Well, I really did want to try it. As a married woman I never expected that I would suggest a man eating me. But my mind accepted something which got me in the room, and then his significant charm allowed me to put my normal feelings aside and make the best of this. So I moved.
I felt very exposed to him as I settled into position, I was exposing my tempting butt and my rosebud to close inspection as I lowered myself on his face. He had to be thinking of how he would put his cock into both of my holes, enjoying himself energetically, and take his release there. Now I willingly giving him my mouth as well. Looking at him I did not see any potential for great danger, which was my first concern. His entry into my ass would likely come last. I realized he would last longer after one or two more conventional climaxes, so maybe the sodomy would last longer if I sucked him off. But on the other hand, given his age I was not sure about his next hard-on even showing up.
He guided me down until I felt the lightest touch of his tongue eagerly running along my labials, tasting me. It was a little thing, but I felt his desire for my pussy ... my body.
I was still straight up, looking at his cock. I thought of the pornos my husband and I watched, where tiny women sucked the seed from giant porno star cocks, swallowing some, and taking facials from others. His cock was smaller than my man’s and he had no giant ridge like Roger. It looked like one that I could easily take it in my mouth or my butt.
“Are you going to remain sitting up? That is fine with me, but I thought...”
“No ... I just wanted to make sure you were okay. Plus, honestly, it is an attractive cock to look at. I have not seen that many.”
“That sounds like a line...” he started to say, “but you know, your obvious relative innocence, whether feigned or sincere, is quite attractive.”
I thought about that for a minute, I could not tell what he meant. But I knew actions trumped words so I bent forward and gently kissing the tip, then moved to take him in, parting my lips and moving lower. That got a gasp from him, cutting off his words. I could smell how he had washed very recently. He was the perfect size for me, as I moved down my lips engulfed his head, taking the low ridge and then the start of his shaft. It flared a little at the ridge, but my lips could feel that the ridge was not that much wider than the shaft. As I took the start of his shaft into my mouth where my tongue licked on his hole and the frenulum. The area was sensitive and it was easy for me to play with. Plus he plainly liked it. I took a little more in, by staying this shallow it was not a strain to actively give pleasure with my tongue and lips.
“That is very nice,” he said. “I don’t usually get oral ... I guess I stopped asking.” He enjoyed my stimulation for a minute or two. “That is very nice work, but I cannot hold back from enjoying this fresh flower in front of me.” With that his tongue carefully started moving to open my labials up and gently licking them as he worked the tip deeper into my valley. He was careful, never touching me in a way that caused me to jump. But he seemed to enjoy the gentle lip and tongue work he was giving me. What is the term I was thinking? Oh yes, we were both “tickling each others fancy,” except we were doing it very gently.
Neither of us could actually mention it, as we both had our mouths full.
Over the next 5 or 10 minutes, I just played with his cock in my mouth, it was stimulating, but it wasn’t really sex for either of us. More like gentle ‘getting to know you’ pleasure. I tried different movements, using my lips and tongue. He was aroused and he clearly liked it, but it did not seem to be moving towards release. Perhaps that was because of his age. I shifted locations, licking around his balls a little. He gasped at the change. But that was not as interesting or playful, and the region was too delicate so I backed off and returned to his shaft, being friendly with my mouth.
On the other end, he did a masterful job of preparing my body for his cock, spreading my labials with his mouth so I was wide open. My fluids started flowing, he seemed to relish my juices. Then he started to spread my vag opening, but he did not go deep, just working around the entrance.
At some point we both grew less active so we stopped more or less together. I lifted myself off his face and settled beside him on the bed, face-to-face.
I felt a little awkward because I did not really feel like kissing him, it really was not a face I wanted to kiss. With my husband kissing after oral sex was part of the routine, it was part of the deal the first time either of us ate the other. With Roger too, we were friends who had been touched and done oral before so it felt like we should kiss again even if the circumstances were different. Kissing was normally part of our arousal.
But with this man there was a barrier to kissing. Maybe it was his age, he seemed older than my father. I liked him well enough, he was charming and was very good at making me feel relaxed even if I was naked with him. Yes, age was part of the barrier, he looked to be twice my age. But the greater barrier was that I knew I was there to earn my pay by letting him fuck both my pussy and my ass when and how he wanted. He was a client, not a friend. It was a nice ageless cock, but what was coming, what he knew we had bargained for, banished any hint of emotional attachment between us.
He was looking at me, and it was pretty obvious what he was considering his next move. I shifted a bit, encouraging his imagination, posing to highlight my good parts, above and below. I knew my tits were the stars of the show. Finally he had a plan worked out.
“My dear,” he began, “if it does not offend you, I would like to finish in what is commonly called the marital position, I confess that those wonderful nipples are going to drive me quickly to the heights. However, before we go there with that body of yours, I would like to start with you bent over, perhaps resting on a pillow set on the table, as I enter your gates of paradise. Does that suit you? I ask about the marital position because of your loss ... I also lost my lover. Because of those memories it was something I avoided ... for a time.”
Well, that was the tale I told him earlier. I thought fast. “For us that position was nice, but it retains no undue emotional weight. He also liked chairs, or me on top, or really just about anything.” I remembered my man saying that when going outside of the legend, it was good to use the truth. “We often moved around, in fact our first time was me on top looking at his feet. It was hardly romantic. I confess that after a time we made a game to changing positions while joined ... he was a very flexible.”
Mr. G barked a laugh, I had surprised him. “I’m afraid these old joints are no longer suited to such delightful games ... But for now...” he motioned towards the table.
I did as he asked, sauntering over to the table in a way that said I knew he was looking at my bottom. I placed a pillow on the edge of the small sturdy wooden table where we negotiated our contract, and settled myself, stretching out with the pillow as a cushion for my hips at the edge while my chest rested on the cool hard surface of the table. I knew that the muscles of my back were arousing. Then I spread my legs and used my hand to spread my labials. “Is the height okay?”
He came up behind me where his hands took possession of my hips. Our heights were a good match, I am five foot six. He was taller than me by an inch or two but he seemed to have short legs so we worked it out well. The table height made it fit, I realized that he had already measured it and us with his eyes. Maybe he used the chair for reference.
He he held my at the ready he took a moment to mention that this bent-over position was his favorite but was usually not practical with tiny escorts. I knew Mia was short, under 5 foot, so this would not have worked for her.
I glanced around the room. Perhaps the back of the couch would work for her, with her feet off the ground. Yes, I can imagine Mia that way, bent over, laughing like a child with her feet dangling off the ground. She was no stranger to plastic surgery, breasts that bordered on D-cups were just the start. More work done on each set of her lips so they were very large and plump. She was rumored to be the best in town.
Mr. G made contact, the head of his cock bringing my attention back to the here and now. We were about to get down to this fucking business. After lining up his tip slipped into me easily, I was very wet with my own juices and his mouthwork had opened my entrance. I considered what I did with Roger as a college relationship, something that was close to the line of infidelity, but it did not seem like that much of a stretch given our past.
But this, by any reasonable standard, was a step beyond what my promised contemplated. We all knew this coupling was over the line, as he pushed his cock into my body I transformed into a paid whore in my body, my heart, and soul. When he put his cock into me it felt like purely infidelity. I knew it when the ridge of his cockhead entered my body. Since his ridge was not prominent the physical line was not obtrusive. But emotionally, I knew a line was crossed, it was the moment I considered myself as a whore, beyond all doubt. That transition didn’t feel good. I steeled myself to accept it only because my husband had needed it, else our friends, neighbors and his co-workers would be at risk. I had my safety net in a few years, but we doubted many others had any such options.
So I accepted it all, along with what would happen in the ‘end.’
He used two more strokes to work the rest of his shaft inside me, until his belly pressed against the curve of my butt. There he held himself, letting us get used to this intimate contract.
I guess he sensed my tense emotions. “You really are new at this, I can tell. I’ll give you a moment on the path,” as he held still.
There was no pain, his size was not an issue. But inside I felt I was doing something I should not be doing. I was glad for the consideration, then said softly, “Thank you for the thought.”
After resting inside for another moment he drew himself out completely, waited a moment, and then slid in again, giving his strokes a unique feeling. I had to moan at the feeling of the re-entry, despite my mental contortions my body was getting turned on by his fucking.
I was very relaxed being with Roger because I had dreamed of him so many times. Besides him there was only my husband ... up to now. It occurred to me that perhaps I was naturally ‘easy’ and just lacked the life experiences and opportunities needed to become a shameless slut for multiple men. I was close to 30 but Mr. G was only the third man to enter my body, I bet that was a low number for many females a decade younger than me. We seemed to have nothing in common, beyond the base economic transaction. Yet here I was, bent over while he enjoyed using my body.
I was getting very wet for him. Was that even natural? Maybe it was genetic.
Was I naturally a slut? I knew both of my parents were. Maybe I just never had the chance, my guy and I bonded as friends well before my body really knew what sex was. Yet now here I was, I considered myself a married woman, but I was sharing my body with a stranger, bent over a getting wet for his use, expecting cruder use before the evening ended and expecting payment after I was intimately soiled. That pretty much said ‘whore’ to me.
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